3α-(2-furanecarbonyloxy)-tropane | 72594-46-8

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 托烷生物碱
• 英文名称: 3α-(2-furanecarbonyloxy)-tropane
• 英文别名: furan-2-carboxylic acid tropane-3endo-yl ester；Furan-2-carbonsaeure-tropan-3endo-ylester；Methylecgonidin
• CAS: 72594-46-8
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: JBTLJHIQAFDIPV-URLYPYJESA-N

物化性质

• 沸点：
  331.1±32.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.06
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  42.68
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3α-(2-furanecarbonyloxy)-tropane 在 1-氯乙基氯甲酸酯 、 碳酸氢钠 、 甲醇 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以81%的产率得到3α-(2-furanecarbonyloxy)-nortropane
  参考文献：
  名称：

  Synthesis of heteroaromatic tropeines and heterogeneous binding to glycine receptors

  摘要：

  Heteroaromatic carboxylic esters of (nor) tropine were synthesized. Tropine esters displaced [(3)H]strychnine binding to glycine receptors of rat spinal cord with low Hill slopes. Two-site displacement resulted in nanomolar IC(50,1) and micromolar IC(50,2) values, and IC(50,2)/IC(50,1) ratios up to 615 depending on the heteroaromatic rings and N-methyl substitution. Nortropeines displayed high affinity and low heterogeneity. IC(50,1) and IC(50,2) values of tropeines did not correlate suggesting different binding modes/sites. Glycine potentiated only the nanomolar displacement reflecting positive allosteric interactions and potentiation of ionophore function. Affinities of three (nor) tropeines were different for glycine receptors but identical for 5-HT(3) receptors. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.08.029
• 作为产物：
  描述：

  呋喃甲酰氯 、 3-tropanol 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以0.58 g的产率得到3α-(2-furanecarbonyloxy)-tropane
  参考文献：
  名称：

  Synthesis of heteroaromatic tropeines and heterogeneous binding to glycine receptors

  摘要：

  Heteroaromatic carboxylic esters of (nor) tropine were synthesized. Tropine esters displaced [(3)H]strychnine binding to glycine receptors of rat spinal cord with low Hill slopes. Two-site displacement resulted in nanomolar IC(50,1) and micromolar IC(50,2) values, and IC(50,2)/IC(50,1) ratios up to 615 depending on the heteroaromatic rings and N-methyl substitution. Nortropeines displayed high affinity and low heterogeneity. IC(50,1) and IC(50,2) values of tropeines did not correlate suggesting different binding modes/sites. Glycine potentiated only the nanomolar displacement reflecting positive allosteric interactions and potentiation of ionophore function. Affinities of three (nor) tropeines were different for glycine receptors but identical for 5-HT(3) receptors. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.08.029

文献信息

• US2824106
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis of heteroaromatic tropeines and heterogeneous binding to glycine receptors
  作者：Gábor Maksay、Zoltán Vincze、Péter Nemes

  DOI：10.1016/j.bmc.2009.08.029

  日期：2009.10

  Heteroaromatic carboxylic esters of (nor) tropine were synthesized. Tropine esters displaced [(3)H]strychnine binding to glycine receptors of rat spinal cord with low Hill slopes. Two-site displacement resulted in nanomolar IC(50,1) and micromolar IC(50,2) values, and IC(50,2)/IC(50,1) ratios up to 615 depending on the heteroaromatic rings and N-methyl substitution. Nortropeines displayed high affinity and low heterogeneity. IC(50,1) and IC(50,2) values of tropeines did not correlate suggesting different binding modes/sites. Glycine potentiated only the nanomolar displacement reflecting positive allosteric interactions and potentiation of ionophore function. Affinities of three (nor) tropeines were different for glycine receptors but identical for 5-HT(3) receptors. (C) 2009 Elsevier Ltd. All rights reserved.